Réaction #577220

Équation de réaction

7-Allyloxy-4-methylcoumarin

N,N-diethylaniline

→

3

Rendement 88.0%

8-Allyl-7-hydroxyl-4-methyl-2H-chromen-2-one

Rendement 88.0%

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was then cooled, during which some of the product
2. 2
   Autreprecipitated
3. 3
   workup.ADDITIONHexane (10 mL) was added in order
4. 4
   Autreto precipitate out the remaining product
5. 5
   FiltrationThe precipitate was filtered
6. 6
   Lavagewashed with hexane
7. 7
   Autredried under vacuum

Mode opératoire

7-Allyloxy-4-methylcoumarin 2 (1.0 g, 4.62 mmol) was dissolved in N,N-diethylaniline (8 mL) in a sealed vial and heated to 250° C. for 25 min under microwave. The reaction mixture was then cooled, during which some of the product precipitated. Hexane (10 mL) was added in order to precipitate out the remaining product. The precipitate was filtered, washed with hexane, and dried under vacuum to yield 3 as a pale-yellow solid (0.88 g, 88%). TLC (hexane/ethyl acetate, 1:3): Rf=0.5. mp 204° C. 1H NMR (CDCl3/CD3OD, 500 MHz) δ 2.43 (s, 3H, CH3), 3.57 (d, J=6.0 Hz, 2H, CH2), 4.95 (d, J=10.0 Hz, 1H), 5.04 (d, J=17.0 Hz, 1H), 5.97 (m, 1H), 6.10 (s, 1H), 6.86 (d, J=9.0 Hz, 1H), 7.46 (d, J=9.0 Hz, 1H). 13C NMR (CDCl3/CD3OD, 125 MHz) δ 18.85, 27.66, 110.78, 113.20, 113.73, 114.93, 115.41, 124.38, 136.16, 153.89, 155.88, 160.18, 163.92. ESIMS calcd for C13H13O3 [M+H]+ 217.1. Found 217.2.

Source